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. 2020 Mar 11;11(14):3629–3635. doi: 10.1039/d0sc00444h

Organocatalyzed Michael addition of acetone to β-nitrostyrenea.

graphic file with name d0sc00444h-u1.jpg
Entry Cat T % convb e. r.c
1 4 NO <5
2 6a NO 55 57 : 43
3 6b NO 28 54 : 46
4 4 YES 17 57 : 43
5 6a YES 85 78 : 22
6 6b YES 95 91 : 9
7 YES 0 0
a

Reaction conditions: acetone (0.25 mmol), β-nitrostyrene (0.025 mmol), catalyst (10 mol%), N-hexylthymine (0 or 0.125 mmol), CH2Cl2 (100 μL), 25 °C, 5 days.

b

Determined by 1H NMR from the crude reaction.

c

e. r. determined by HPLC using a Daicel ChiralPak AS-H column.